Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 423-431.DOI: 10.6023/cjoc201909007 Previous Articles     Next Articles


张萍a,c, 石浩楠b, 张天舒a, 蔡佩君a, 姜波b, 屠树江b   

  1. a 中国矿业大学化工学院 江苏徐州 221116;
    b 江苏师范大学化学与材料科学学院 江苏徐州 221116;
    c 江苏省徐州医药高等职业学校 江苏徐州 221116
  • 收稿日期:2019-09-04 修回日期:2019-10-16 发布日期:2019-10-25
  • 通讯作者: 蔡佩君, 屠树江;
  • 基金资助:

Alkynylphosphonation of Unactivated Olefins via Radical-Triggered 1,2-Alkynyl Migration

Zhang Pinga,c, Shi Haonanb, Zhang Tianshua, Cai Peijuna, Jiang Bob, Tu Shujiangb   

  1. a School of Chemical Engineering&Technology, China University of Mining and Technology, Xuzhou, Jiangsu 221116;
    b School of Chemistry&Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116;
    c Jiangsu Provincial Xuzhou Pharmaceutical Vocational College, Xuzhou, Jiangsu 221116
  • Received:2019-09-04 Revised:2019-10-16 Published:2019-10-25
  • Supported by:
    Project supported by the Fundamental Research Funds for the Central Universities (No. JH180263).

A silver-mediated alkynylphosphonation of 1,4-enynes with diarylphosphine oxides has been developed, by which a wide range of γ-ketophosphine oxides with moderate to good yields were synthesized through radical 1,2-alkynyl migration. The transformation proceeded with sequential P-centered radical addition to vinyl unit, 3-exo-dig cyclization and 1,2-alkynyl migration, resulting in the bond-forming events including C-P and C-C bonds to realize difunctionalization of unactivated olefins.

Key words: 1,4-enynes, alkynylphosphonation, γ-ketophosphine oxides, alkynyl migration, radical chemistry